Absolute Configuration of 2,7-Diazaspiro[4.4]nonane. A Reassignment

Journal of Organic Chemistry

Volumn 46, Issue 13, 1981, Pages 2757-2764

  Overberger, C G ^a   Wei Wang, David ^a   Hill, Richard K ^b   Krow, Grant R ^b   Ladner, David W ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006955478     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00326a031     Document Type: Article

References (20)

1. The portion of this work performed by Dr. Krow was carried out at Princeton University, Princeton, NJ.
2. G. Krow, Top. Stereochem., 5, 31-68 (1970).
3. G. Krow and R. K. Hill, Chem. Commun., 430-431 (1968).
4. For proof of absolute configuration, see M. E. Cox, G. A. Ellestad, J. Hannaford, I. R. Wallwork, W. B. Whalley, and B. Sjoberg, J. Chem. Soc., 7257-7260 (1965).
5. S. Ställberg-Stenhagen, Arkiv. Kemi, 3, 273-280 (1951).
6. Imide 13 is the antiepileptic agent ethosuximide [A. Spinks and W. S. Waring, Prog. Med. Chem., 3,261-331 (1963)] and this preparation from (S)-12 constitutes a proof of its absolute configuration.
7. J. Knabe and J. Plisch, Tetrahedron Lett., 745-746 (1973).
8. R. S. Cahn, C. Ingold, and V. Prelog, Angew. Chem., Int. Ed. Engl., 5, 385-415 (1966); see especially example 31 on p 397.
9. In the original assignment of ref 3, the configuration was based on the rides of axial chirality rather than central chirality. According to the sequence rules of axial chirality, the spiranes (-)-l and (+)-2 could be designated as S configuration. For a detailed discussion, see D. W. Wang, Ph.D. Dissertation, The University of Michigan, Ann Arbor, MI, 1979.
10. G. Casini, O. Cicchetti, and M. Ferappi, Ann. Chim., 51,366-374 (1961); Chem. Abstr., 55, 27051 (1961).
11. J. A. Dale, D. L. Dull, and H. S. Mosher, J. Org. Chem. 34, 2543-2549 (1969).
12. G. Lowe, Chem. Commun., 411-413 (1965).
13. J. H. Brewster and R. S. Jones, Jr., J. Org. Chem., 34, 354-358 (1969).
14. H. Wynberg and J. P. M. Houbiers, J. Org. Chem., 36, 834-842 (1971).
15. J. H. Brewster and R. T. Prudence, J. Am. Chem. Soc., 95, 1217-1229 (1973).
16. R. K. Hill and D. A. Cullison, J. Am. Chem. Soc., 95, 1229-1239 (1973).
17. X. A. Dominguez, I. C. Lopez, and R. Franco, J. Org. Chem., 26, 1625 (1961).
18. We are indebted to Dr. B. R. Franko-Filipasic and Mr. W. J. McCarthy of the FMC Corporation for carrying out large-scale reductions.
19. C. Klinke, Chem. Abstr., 63, 15267 (1965).
20. M. Kojima, T. Kawakita, and K. Kudo, Yakugaku Zasshi, 92, 465-470 (1972); Chem. Abstr., 77, 34230 (1972).